1. Field of the Invention
The field of organic chemistry is continuously evolving new methods for introducing functionalities into hydrocarbons. Because of the wide range of utilities possessed by amines and their derivatives alternative routes for introducing amine functionalities are always desirable.
2. Description of the Prior Art
The use of hydrocyanic acid with alcohols or olefins has been reported in the literature, frequently under the title of the Ritter reaction. For a review, see Zila's Berman, Russ Chem. Rev. 29, 331-344 (1960).
Potts et al, U.S. Pat. Nos. 3,338,967 and 3,530,153, describe a process for the preparation of secondary-alkyl primary amines by the reaction of an olefin with hydrocyanic acid and water in a hydrogen fluoride medium. This process yields a formamide intermediate rather than an N-hydrocarbyl formimidate ester. U.S. Pat. Nos. 3,402,193, 3,374,260, and 3,580,943 describe the reaction of alcohols or mercaptans with HCl or HBr and a nitrile (Pinner synthesis) which proceeds via the protonation of nitrile rather than the alkylation of HCN and yields imidates other than formimidate esters. The Pinner synthesis can only produce N-unsubstituted imidates. N-substituted imidates are produced from imidoyl derivatives by alcoholysis or reaction with sodium alkoxide, or by alkylation of imides or thionamides by alkyl halides, sulfates or oxonium salts. See P. A. S. Smith, Open-Chain Nitrogen Compounds, Vols. I and II, W. A. Benjamin, New York.